Electric Literature of 58313-23-8, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 58313-23-8 name is Ethyl-3-iodobenzoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.
A dry and argon-flushed round-bottomed flask equipped with a magnetic stirring bar was charged with ethyl 3-iodobenzoate (178 mg, 0.64 mmol, 3.75 eq.) in dry THF (1.0 mL) and cooled to -20 C. A solution of isopropylmagnesium chloride-lithium chloride complex (1.3M in THF, 0.33 mL, 0.43 mmol, 2.5 eq.) was added dropwise and the resulting mixture was stirred at – 20 C for 1 h. To the reaction mixture, was then added aldehyde 5 [13] (56 mg, 0.17 mmol) as a solution in THF (0.5 mL, rinsed with an additional 0.5 mL), and the mixture was stirred at – 20 C for 25 min. The reaction was quenched by adding methanol (0.5 mL) and diluting with water (5 mL). The whole mixture was extracted with ethylacetate (20 mL x 3). The combined organic layers were washed with brine (5 mL), dried over sodium sulfate and filtered. Evaporation of the filtrate afforded a residue, from which 6a (68 mg, colorless solid, 86%) was separated by silica gel column chromatography (ethyl acetate: n-hexane 1: 15) as a C22-epimeric mixture (77:23). 6a: 1H NMR (400 MHz, TMS, CDCl3) d – 0.01 (6H x 0.23, s), 0.01 (6H x 0.77, s), 0.70 (3H, d, J 6.8 Hz), 0.88 (9H x 0.23, s), 0.90 (9H x 0.77, s), 0.95 (3H x 0.77, s), 0.96 (3H x 0.23, s), 1.40 (3H, t, J 7.1 Hz), 3.97 (1H x 0.23, s), 4.03 (1H x 0.77, m), 4.38 (2H, q, J 7.2 Hz), 4.89 (1H x 0.23, d, J 3.2 Hz), 4.98 (1H x 0.77, s), 7.41 (1H, t, J 7.7 Hz), 7.51 (1H, d, J 7.7 Hz), 7.92 (1H, d, J 7.7 Hz), 7.95 (1H x 0.77, s), 8.00 (1H x 0.23, s); HRMS (ESI) m/z calcd. for C28H46O4SiNa [MNa] 497.3058, found 497.3060.
At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl-3-iodobenzoate, and friends who are interested can also refer to it.